Methyl Acrylate → Heptanedioic acid, 4-cyano-4-(1-naphthalenyl)-, dimethyl ester

HRID 1576198Notes

Reaction equation

HRID 1576198 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>C(O)(C)(C)C>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][C:11]([C:12]#[N:13])([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 85961-Naphthaleneacetonitrile

Product 1

HCID 12230233Heptanedioic acid, 4-cyano-4-(1-naphthalenyl)-, dimethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 20.9 g. (0.125 mole) of the known compound (1-naphthyl)acetonitrile and 58 ml. of methyl acrylate in 60 ml. of t-butyl alcohol is heated to reflux. The heat is removed and 19 ml. of 40% methanolic Triton B in 28 ml. of t-butyl alcohol quickly added. After about 4 hours of heating at refux the mixture is allowed to cool and taken up in water and benzene. The organic layer is washed successively with 2.5 N hydrochloric acid, water and brine and then evaporated to dryness. The residue is distilled under vacuum, first at 40 mm. of mercury to remove excess methyl acrylate and then at 0.5 mm. to give 24.96 g. (59% yield) of dimethyl-4-cyano-4-(1-naphthyl)pimelate, having a boiling point of 209° to 219°C. The NMR spectrum of the compound confirms its expected structure.

Workup

  1. additionA mixture of 20.9 g
  2. customThe heat is removed
  3. additionof t-butyl alcohol quickly added
  4. temperatureAfter about 4 hours of heating at refux the mixture
  5. temperatureto cool
  6. washThe organic layer is washed successively with 2.5 N hydrochloric acid, water and brine
  7. customevaporated to dryness
  8. distillationThe residue is distilled under vacuum, first at 40 mm
  9. customof mercury to remove excess methyl acrylate
  10. customto give 24.96 g

Sources & evidence

ORD record
ord-beeaf997130f4f92863b027f8d2e1999
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

Loading…